Oakley Hall's sound has been described as psychedelic roots music that reconsiders traditional Americana by locating its rainbows at the root. The songs on Second Guessing are filled with co-ed harmonies, intricately woven guitar and fiddle lines, and percussion that romps and rocks. The album has already been described by Mike Wolf of Time Out New York as conjuring the "untamed sound of country rock." This Oakley Hall's second full-length is aptly titled in that it both continues and questions some of the musical themes that appeared on their debut (released on Bulb). The band's current configuration rocks harder and with more pathos than most projects riding today's revivalist wave.